Separation of alk(en)ylresorcinols from rye bran with saturated, monoenoic, dienoic, trienoic and hydroxylated monoenoic side chains using an octyl phase in ultra-high performance liquid chromatography and their differentiation by tandem mass spectrometrie

Zimmermann, Benno F.; Patzke, Hannes; Schieber, Andreas

doi:10.1016/j.chroma.2017.05.032

Cited by 10 publications

(11 citation statements)

References 21 publications

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“…a Numbering based on CCC elution order (Fig. 4) b Trace amounts, contribution < 0.1% to the total alkylresorcinols content c Several isomers; GC retention time indicates the amount of isomers with the position of double bond Finally, CCC fractionation enabled the detection of traces of five odd-numbered triunsaturated ARs including AR17:3 to AR23:3 (previously described in rye [6]) along with AR25:3 (Table 2). Unfortunately, positions and configurations of the double bonds could not be determined with the DMDS adduct method (data not shown).…”

Section: Alkylresorcinols With Unsaturated Alkyl Chains (Alkenylresormentioning

confidence: 94%

“…Aliquots (~0.1 mg) of selected CCC fractions (6,7,10,16,24) were placed in a 1.5-mL vial and supplemented with 50 μL acetic anhydride and 100 μL pyridine [18]. The sealed vial was heated to 60°C for 2 h and at the end of the reaction, the solvent was removed by a gentle stream of nitrogen at 40°C.…”

Section: Preparation Of Acetylated Alkylresorcinol Derivativesmentioning

confidence: 99%

“…Samples were prepared according to the protocol of Buser et al [20] with slight modifications. An aliquot (~200-μg sample of selected CCC fractions 6,7,10,14,16,22,24,38 and 59, respectively) was dissolved in 50 μL n-hexane in a 2-mL vial. After addition of 100 μL DMDS and 10 μL iodine solution (6% iodine in diethyl ether), the vial was sealed with a cap and heated to 60°C for 24 h [20].…”

Section: Preparation Of Dimethyl Disulfide Adducts Of Alkylresorcinolsmentioning

confidence: 99%

“…High-performance liquid chromatography with tandem mass spectrometry (HPLC/MSMS) [6] and gas chromatography with mass spectrometry (GC/MS) analyses [7] showed that 85% of the ARs in rye feature a saturated alkyl chain (ARn:0) [8]. The most relevant representatives are odd-numbered (AR17:0-AR25:0) along with low shares of AR15:0 and AR27:0 and even-numbered homologues (AR16:0-AR24:0) [6,9]. The remaining share of~15% constitutes mainly of mono-(ARn:1), di-(ARn:2) and tri-(ARn:3) unsaturated hydrocarbon chains (alkenylresorcinols).…”

Section: Introductionmentioning

confidence: 99%

“…The remaining share of~15% constitutes mainly of mono-(ARn:1), di-(ARn:2) and tri-(ARn:3) unsaturated hydrocarbon chains (alkenylresorcinols). In addition, hydroxyl (ARn:1-OH) and keto (ARn:0 oxo) groups can be present as substituents on the alkyl chain [6,7,10].…”

Section: Introductionmentioning

confidence: 99%

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Countercurrent chromatographic fractionation followed by gas chromatography/mass spectrometry identification of alkylresorcinols in rye

2020

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Alkylresorcinols (5-alkyl-1,3-dihydroxybenzenes, ARs) are bioactive phenolic lipid compounds which are particularly abundant in rye and partly other cereals. In this study on ARs, whole rye grain extracts were gained with cyclohexane/ethyl acetate (46/54, w/w). Silylated extracts were used to develop a gas chromatography with mass spectrometry method in the selected ion monitoring mode (GC/MS-SIM) for the sensitive detection of conventional ARs along with keto-substituted (oxo-AR) and ring-methylated ARs (mAR) with 5-alkyl chain lengths of 14 to 27 carbon atoms and 0 to 4 double bonds in one run. Analysis was performed by countercurrent chromatographic (CCC) fractionation using the solvent system n-hexane/ethyl acetate/methanol/water (9/1/9/1, v/v/v/v). Subsequent GC/MS-(SIM) analysis of 80 silylated CCC fractions enabled the detection of 74 ARs in the sample. The CCC elution of the ARs followed the equivalent chain length (ECL) rule in which one double bond compensated the effect of two (additional) carbon atoms. Novel or rarely reported ARs were detected in virtually all classes, i.e. saturated AR (AR14:0), even-numbered monounsaturated AR isomers (AR16:1-AR26:1), triunsaturated ARs (AR25:3), oxo-ARs (AR17:0 oxo, AR19:1 oxo, AR21:2 oxo, AR23:2 oxo) and odd-numbered methyl-ARs (mAR15:0-mAR23:0). Positions of the double bonds of monounsaturated ARs and oxo-ARs were determined with the help of dimethyl disulfide (DMDS) derivatives.

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Section: Alkylresorcinols With Unsaturated Alkyl Chains (Alkenylresormentioning

confidence: 94%

Section: Preparation Of Acetylated Alkylresorcinol Derivativesmentioning

confidence: 99%

Section: Preparation Of Dimethyl Disulfide Adducts Of Alkylresorcinolsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Countercurrent chromatographic fractionation followed by gas chromatography/mass spectrometry identification of alkylresorcinols in rye

2020

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Distribution of cereal phytochemicals and micronutrients in whole grains: A review of nutraceutical, industrial, and agricultural implications

Nguyen,

Drawbridge,

Beta

2024

Cereal Chem

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Background and ObjectivesThere is mounting evidence that whole cereal grains are a source of many micronutrients and phytochemicals that confer several health benefits. This work aimed to investigate the distribution patterns and related implications of selected bioactive compounds from various cereal grains and discuss the techniques used to study their distribution.FindingsHand dissection and imaging techniques are the methods used to locate bioactive compounds in whole grains with high accuracy. Pearling and milling are methods of industrial importance. Phenolic compounds are concentrated in cereal bran, whereas the germ is rich in carotenoids and tocols (particularly tocopherols). Knowing the distribution pattern of compounds allows a better understanding of their bioaccessibility and associated bioactivity, as well as developing means to recover them and enhance their occurrence in the aleurone layer.ConclusionsGradient patterns exist in the distribution of phytochemicals and micronutrients derived from cereal grains. This knowledge can be translated into a number of purposeful and practical applications.Significance and NoveltyThis study employed a comparative approach to examine the repartition of various compounds in whole grains of assorted cereals with an emphasis on minor crops. The implications are relatable and applicable in diverse sectors to ultimately improve the well‐being of cereal consumers.

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Isolation of saturated alkylresorcinols from rye grains by countercurrent chromatography

Hammerschick

Wagner

Vetter

2021

J of Separation Science

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Alkylresorcinols (5-alkyl-1,3-dihydroxybenzenes) are amphiphilic phenolic lipid compounds that are abundant in cereals with highest contents in rye. Alkylresorcinols are suspected to show a wide range of favourable biological activities.For such and further testing, highly pure alkylresorcinol standards are required. Especially, purities >> 98% were partly difficult to obtain in the past. Here, we aimed to isolate the most abundant (saturated) alkylresorcinols from rye using countercurrent chromatography. To achieve very high purity, alkylresorcinolcontaining extract (∼7.14 g) of rye grains (cold extracts with cyclohexane/ethyl acetate (46/54, w/w)) were preparatively transesterified followed by a preparative hydrogenation. Countercurrent chromatography separation of ∼1 g hydrogenated and transesterified rye grain extract using the solvent system n-hexaneethyl acetate-methanol-water (9:1:9:1, v/v/v/v) yielded 51.8 mg AR17:0, 77.4 mg AR19:0, 57.2 mg AR21:0, 28.8 mg AR23:0 and 11.5 mg AR25:0 with purities >99% in either case. The isolated alkylresorcinol homologues can be used for subsequent bioassays.

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Separation of alk(en)ylresorcinols from rye bran with saturated, monoenoic, dienoic, trienoic and hydroxylated monoenoic side chains using an octyl phase in ultra-high performance liquid chromatography and their differentiation by tandem mass spectrometrie

Cited by 10 publications

References 21 publications

Countercurrent chromatographic fractionation followed by gas chromatography/mass spectrometry identification of alkylresorcinols in rye

Countercurrent chromatographic fractionation followed by gas chromatography/mass spectrometry identification of alkylresorcinols in rye

Distribution of cereal phytochemicals and micronutrients in whole grains: A review of nutraceutical, industrial, and agricultural implications

Isolation of saturated alkylresorcinols from rye grains by countercurrent chromatography

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